Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

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Valued Stay Sun Prairie

Valued Stay Sun Prairie

2.5 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in and express check-out are also provided.
The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
A full-service spa, a hot tub, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Unwind with a drink at one of the 4 bars/lounges and enjoy perks like a free area shuttle.
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

2 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like self-serve breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Cambria Hotel Madison East

Cambria Hotel Madison East

3 out of 5
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Madison (MSN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Top Windsor hotels deals

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave, Madison, WI
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr, Madison, WI
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Moxy Madison Downtown

Moxy Madison Downtown

3.5 out of 5
823 East Washington Ave, Madison, WI
Free Cancellation
Reserve now, pay when you stay
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A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
525 West Johnson Street, Madison, WI
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a terrace are also offered.
Free airport shuttle
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Cool street art in Madison, Wisconsin

University of Wisconsin-Madison

4.5/5(872 reviews)

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Great place to check out the sunset and hang out with friends and family!

Monona Terrace Community and Convention Center

4.5/5(164 reviews)

Learn about the events happening at Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Monona Terrace Community and Convention Center
Capitol Building

Capitol Square

4.5/5(710 reviews)

You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.

Capitol Square

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity provides flight and hotel vacation packages starting from just $493. With such huge savings, you'll be exploring all of Windsor in a flash.
How long should my Windsor vacation be?
Many travelers choose to spend about 2 nights in Windsor, but it's your call. If you want to venture out and explore all the exciting things this location has waiting for you, why not hang around another night or two?
Where can I get the best vacation package deals for Windsor?
It's difficult to beat Travelocity when it comes to finding your Windsor package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to select from. Reserve your trip now and get ready to cross another exciting place off your must-visit list.
Why should I purchase my Windsor vacation package via Travelocity?
By booking your hotel, flights, activities and car rental all in the one place, you'll save both time and money. All our bookings come with round-the-clock customer support, and you'll know that you'll always score the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book the vacation of your dreams today and get packing!
Can I save on my Windsor car rental if I combine it with a hotel or flight?
Certainly --- bundle your car, flight and hotel into a Windsor vacation package and you'll save a ton. With so much to uncover in the Windsor area, that set of wheels will make exploring a joy. Once you've slid into the driver's seat, get out on the wide open road and cruise toward Wrigley Field, a top sight around 120 mi from Windsor.
Which airport is best for Windsor?
The most convenient airport for Windsor is Dane County Regional Airport (MSN). You'll find it 6 mi north of the city center.
What is there to do in Windsor?
Mousehouse Cheesehaus should be on your travel schedule. After you've checked off this top attraction, simply stroll the streets of Windsor and get a feel for what makes this fantastic destination tick.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

Photo by Joel Holland
Photo by Joel Holland